Essos – Pentos
"Third," Illyrio went on like a professor who had already mapped out every move, "we reform the conscription system and build a real standing army instead of scraping together temporary levies every time trouble shows up."
He laid everything out with perfect precision, hitting every nerve in the room exactly right.
(All of it thanks to one of his behind-the-scenes advisors—a Braavosi maester Illyrio had quietly started treating like a full Citadel archmaester.)
"Farmers and sellswords yanked off the street for a season have zero fighting value. On a real battlefield they're just meat for the grinder. Why waste grain feeding men who'll break and run the first time blood hits the dirt?"
Illyrio spread his hands and pointed straight at Harry Strickland.
"But if we had an army on the same level as the Golden Company, our supply costs would drop dramatically—and that army could stop the Dothraki cold before they ever reached our walls!"
The others weren't smirking anymore. They were thinking hard, turning Illyrio's words over in their minds.
They finally understood: the fat Magister had come to this meeting fully armed.
"Fourth," Illyrio continued, "we expand the navy and start building an entirely new generation of warships."
"Warships…"
"A new generation?!"
That one made several Magisters sit up straight. In their minds, Braavos's great galleys and the Summer Isles swan ships were already the gold standard.
But the way Illyrio said it, he clearly had something better.
"I have a friend who possesses the plans for a revolutionary new warship. It uses an entirely new propulsion system. Even sailing directly into the wind, it can furl its sails and still move under its own power…"
The room stirred. These men weren't fools, but none of them had ever heard of anything like it.
"This… this is impossible…"
"Magic?"
Illyrio swept his gaze across every face, drinking in their reactions.
"If the plan succeeds, I will personally sail one of the prototypes I've already acquired right into our harbor and demonstrate it for you. The only drawback is the high cost—and it does require a special 'energy source' supplied by my friend."
The scales tipped even further in Illyrio's favor. Everyone understood that a fleet of ships like that would give Pentos a crushing edge in any naval battle.
"Fifth…"
Illyrio paused for dramatic effect, then dropped the real bomb: "Fifth, we suspend the non-militarization treaty with Braavos. That paper shackles our fleet and army size and leaves us helpless when real threats appear."
Marco Volaris shot to his feet. "You've gone mad! Braavos will treat this as a declaration of war! Their navy is the strongest in Essos. If they think we're challenging their control of the sea—"
"Braavos has its own problems right now," Illyrio said calmly. "Their Iron Bank has taken heavy losses on Westerosi investments. Their internal politics are unstable. And most importantly, they also fear the Dothraki. If we expand our forces under the banner of 'joint defense against the horse-lords,' Braavos won't push back too hard. They don't want to watch the Dothraki burn Pentos and then turn north toward them next."
Gino Ferrari stroked his chin. "So your plan is to use the Dothraki threat as cover to rearm completely while loosening Braavos's grip on us."
"Not only that," Illyrio's eyes glittered with naked ambition. "This is our chance, gentlemen—a chance to redraw the entire power structure inside Pentos."
He looked around the table. "Our current system is too fragmented. Magisters act alone, merchant guilds do whatever they please, and the military is a disorganized mess. When crisis hits, we react too slowly and we have no leverage at the negotiating table."
Pentos's council-style government was the same across all nine Free Cities, and it had crippled decisive action for centuries.
That was exactly why Illyrio had once thrown so much support behind the Targaryen siblings—the system boxed him in too tightly.
But after listening to his advisor's ideas, Illyrio had found a different path: one that would completely reshape the city's power balance.
"But if we possess a strong, unified military force—if we hold the sword—then we no longer need to bargain with every faction."
Lucio Renaer's expression shifted. As former naval commander, he understood military power better than anyone, but he also heard the deeper threat hidden in Illyrio's words.
"You mean," Lucio said slowly, "anyone who opposes reform, anyone who wants to keep things exactly as they are…"
"Will be left behind by history," Illyrio finished gently, though the ice in his voice was unmistakable. "I'm not talking about coups or purges, gentlemen. I'm simply saying that when the storm hits, everyone aboard the ship must obey the captain's orders—or the whole vessel sinks. Those who refuse to follow… perhaps they should remain safely on shore."
The atmosphere in the chamber turned sharp. The four Magisters exchanged quick glances, weighing risks and rewards.
Marco Volaris represented the most conservative merchant interests. He feared reform would wreck trade, triple military spending would crush the economy, and conflict with Braavos would bring disaster.
Lucio Renaer understood the military necessity but worried about concentrating too much power in one place—he had seen too many generals become tyrants.
Gino Ferrari was ambitious. He saw opportunity: a new power structure could let rising stars like him leap over the old families.
Harry Strickland, the outsider, simply watched in silence.
The Golden Company needed a new long-term patron. Pentos was perfect—rich, strategically placed, facing genuine threats.
And if Harry could plant the Company here permanently, his own power would reach heights no previous commander had ever touched.
"I need time to consider," Marco Volaris said at last. "This is no small decision."
"Of course," Illyrio smiled. "We all have time. But I must remind you—the Dothraki will not wait. Khal Drogo's khalasar is gathering. Scouts say they may ride south next spring. If we are not ready…"
He let the threat hang in the air: without reform, Pentos could face annihilation.
"One last question," Lucio Renaer said. "Even if we agree, where does the gold come from? Tripling the military budget, expanding the navy, recruiting and training new troops… this will cost a fortune. Pentos is wealthy, but not bottomless."
Illyrio's smile turned mysterious. "I already have a solution for the funding. But that discussion comes after we reach basic agreement."
He paused, then added, "I can give you one hint: the solution lies in Westeros. That continent is brewing a storm… and storms always create opportunities."
Gino Ferrari's eyes lit up. He had long heard rumors that Illyrio had secret investments across the Narrow Sea. It seemed the rumors were true.
The meeting dragged on another hour—details debated, objections raised, boundaries tested.
In the end, no formal pact was signed, but the Magisters agreed to form a special committee to study Illyrio's proposals and deliver a report within one month.
Once the others had filed out, only Illyrio and Harry Strickland remained.
"What's your honest read?" Illyrio asked, the merchant smile gone. Only cold calculation remained.
Harry drained his cup. "Volaris will fight you to the end unless you convince him his commercial interests stay safe. Renaer can be brought around if you give him real military authority. Ferrari will back you—but he'll want a big slice of the new power."
Illyrio nodded. "Matches my own assessment. So, Commander—what about the Golden Company? Will you throw your full weight behind this?"
Harry looked at the fat Magister. For the first time a real smile touched his scarred face, twisting the old wound into something almost savage.
"Illyrio, the Golden Company has served many masters, but we rarely get invited to reshape an entire city-state. It's interesting. Challenging. And if we succeed, we stop being just another mercenary band. We become the protectors—and the architects—of a city."
He rose and walked to the window, gazing at Pentos's glittering night skyline. "My ancestors followed the Blackfyres into exile. For a century we've fought to return to Westeros. But perhaps… perhaps it's time to consider a different future. A future here in Essos, with roots of our own."
Illyrio's eyes narrowed. "You're very direct, Commander."
Harry didn't know the full truth of Illyrio's deeper connections. He simply saw a mutually beneficial deal.
"Directness is the foundation of good contracts," Harry replied, turning back. "You need our swords. I need your gold and your harbors. We can lift each other up. But I have one condition."
"Name it."
"If we're reforming Pentos's military, the Golden Company must be the core—not advisors, not auxiliaries, the core. Our officers take key commands. Our training methods become standard. Our doctrine sets the rules."
Illyrio thought for a moment, then nodded slowly. "Agreed. But one condition in return: your soldiers swear loyalty to Pentos, not merely to the Company. I will not tolerate a state inside the state."
Harry smiled. "Loyalty is a flexible word, Magister. We can find wording both sides accept. After all, our motto is 'Gold in the hand.' We never break a signed contract."
The two men stared at each other, measuring, calculating. Two sharp, ruthless, ambitious men who both saw the enormous prize—and the danger.
Finally Illyrio offered his hand. "Then we have a preliminary understanding?"
Harry clasped it firmly. "We do. But many details still need hammering out. Many details."
"Naturally," Illyrio released his grip. "Now let's talk funding. The Westerosi opportunity I mentioned…"
He walked to a locked cabinet, pulled out a rolled parchment, and spread it across the table. It was a detailed map of Westeros, marked in several colored inks.
"According to my latest intelligence," Illyrio said, tapping the map, "the Iron Throne's succession rights may soon be thrown into open dispute. If that happens, Westeros will tear itself apart in civil war. And civil wars always need… outside backers."
Harry studied the map, eyes gleaming beneath his scar. "You mean we play both sides and collect payment from everyone?"
"Something more elegant," Illyrio smiled. "We back the side most likely to win—or the one that offers us the greatest future returns. And I happen to have several very promising… investment targets."
His finger traced across the map and stopped at two locations: Dragonstone and Crackclaw Point.
"Interesting picks," Harry noted. "One is a sidelined royal prince. The other is a brand-new lord who struck it rich overnight."
"But both have real potential, real ambition… and special ties to me," Illyrio said. "More importantly, both face serious cash shortages. Both need outside support. And we can provide that support—in exchange for very favorable future terms."
He looked up. "Picture it, Commander. If Pentos commands a powerful army, if we have reliable allies in Westeros, if the Dothraki threat is neutralized… then Pentos stops being just another Free City. We become a true power—a player capable of shaping events across Essos and even Westeros."
Harry was silent for a long time, weighing the vision. Then he gave a slow nod. "It is a grand vision. But also an extremely dangerous road."
"All great endeavors are dangerous," Illyrio said quietly. "The only question is—do you have the courage to walk it?"
Outside the window, Pentos lay peaceful under the night sky. City lamps twinkled. The harbor lighthouse cut through the sea mist, guiding ships safely in and out. The city looked calm, prosperous, and utterly secure.
Yet inside the most luxurious mansion in the city, two men were quietly plotting a revolution—one that could reshape Pentos, shake all of Essos, and eventually reach across the Narrow Sea to Westeros itself.
Both men believed they were the ones holding the reins.
Neither realized the script had been written long ago—and they were simply playing the roles someone else had already assigned them.